Dimethylformamide → 2-(3-Methylisoxazol-5-yl)acetyl chloride

HRID 419840Notes

Reaction equation

HRID 419840 reaction equation
CN(C)C=O.[C:6](Cl)(=O)[C:7]([Cl:9])=[O:8].[CH3:12][C:13]1[CH:17]=[C:16](CC(O)=O)[O:15][N:14]=1>ClCCl>[CH3:12][C:13]1[CH:17]=[C:16]([CH2:6][C:7]([Cl:9])=[O:8])[O:15][N:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acid

Product 1

HCID 123668732-(3-Methylisoxazol-5-yl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylformamide (few drops), followed by oxalyl chloride (9.5 mL, 106 mmol) were added dropwise to a cooled (10° C.) solution of (3-methyl-isoxazol-5-yl)-acetic acid (5 g, 35.4 mmol) in dichloromethane (50 mL), and the solution was allowed to warm to room temperature. The reaction was stirred for a further 3 hours, then concentrated under reduced pressure. The residue was azeotroped with toluene to afford the title compound.

Workup

  1. additionwere added dropwise to
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-753224ec632142f88bb9041e2c1d35b4
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Reaction notes

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